Hotels near Pleasant Square Ossining

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Where to stay near Pleasant Square?

A hotel room with a large bed, two bedside lamps, a nightstand, a blue chair, and a view of greenery through the window.

A modern interior with seating areas, tables, and artwork on the walls.

A spacious indoor area with large windows, modern furniture, and a view of a landscaped outdoor area.

A conference room with a large screen displaying a building image, a whiteboard, and a table with laptops, papers, and coffee cups.

1. Windrose On Hudson

3.1 km from Pleasant Square

tiffany

$213

$237 total

includes taxes & fees

Sep 27 - Sep 28

A spacious living room with a large window, a ceiling fan, a dining area with a table and chairs, and a staircase leading to an upper level.

A large, two-story house with a prominent front entrance, multiple windows, and a driveway.

A swimming pool with lounge chairs and a wooden deck, surrounded by trees and a building with a sloped roof.

A modern living room with a sectional sofa, a coffee table, and large windows offering a view of trees.

2. Summer Pool Oasis Custom Bar Arcade Pool Table

0.7 km from Pleasant Square

$659

$1,233 total

includes taxes & fees

Sep 15 - Sep 16

A hotel room with a wooden headboard, a bedside table with a lamp, and a bed with white bedding and pillows.

A sign for Ardsley Acres Hotel Court with a landscaped garden in the background.

A reception area with a wooden reception desk, a bulletin board with various items, and an exit sign.

A motel with a gazebo in the front lawn, a signboard, and several parked cars.

3. Ardsley Acres Hotel Westchester

17.1 km from Pleasant Square

Gail

$112

$128 total

includes taxes & fees

Sep 17 - Sep 18

A modern lobby with seating areas, a fireplace, and a flat-screen TV mounted on the wall.

A spacious hotel lobby with a modern design, featuring a central seating area with sofas and armchairs, a coffee table, and a television.

A modern bar area with a bar counter, seating, and a colorful mural.

A modern lobby with a reception desk, seating area, and a decorative wall.

4. Cambria Hotel & Suites - White Plains Downtown

16.5 km from Pleasant Square

Lacey

$203

$232 total

includes taxes & fees

Sep 27 - Sep 28

An outdoor seating area with modern furniture, a fire pit, and ambient lighting.

A modern bar area with a long counter, multiple stools, and a bar stocked with bottles.

A modern lobby with a large, tufted sofa, two armchairs, and a wooden coffee table. There are tall, cylindrical columns and a decorative wall with a geometric pattern.

A hotel entrance with a glass door, a blue-lit entrance, and a skylight above.

5. Sonesta White Plains Downtown

17 km from Pleasant Square

Christina

$162

$219 total

includes taxes & fees

Oct 4 - Oct 5

A stone building with a tower, surrounded by a garden with large rocks and various plants.

A room with wooden rocking chairs, a coffee maker, and a view of trees through large windows.

A stone fire pit with flames, surrounded by benches and a building with large windows in the background.

A hotel room with two beds, a dining area with a table and chairs, a TV mounted on the wall, and a large window with a view of trees.

6. The Abbey Inn & Spa

15.6 km from Pleasant Square

"Great stay at the Abbey Inn. Truly elevated and serine. The staff was very helpful with our requests and accommodated perks that were very appreciated by our family. We traveled with 2 kids and the team went above and beyond for us. The on site restaurant was also great as well as the pool and sunroom. Sunset cookies and tea were a nice touch as well as S’mores on the property as well. Would highly recommend."

Yevgeniy

$401

$504 total

includes taxes & fees

Oct 12 - Oct 13

A spacious interior with a high ceiling, stone walls, and modern furniture.

A spacious corridor with stone walls, large windows, and a central chandelier.

An indoor swimming pool with a wooden ceiling and brick walls.

A modern building with a stone facade and wooden beams, surrounded by a well-maintained lawn and trees.

7. Sleepy Hollow Hotel, a Dolce by Wyndham

11.3 km from Pleasant Square

Morgan

$137

$157 total

includes taxes & fees

Sep 28 - Sep 29

A modern high-rise hotel with a curved facade, multiple floors, and a well-lit entrance.

A modern lounge area with sofas, armchairs, a coffee table, and a fireplace.

A modern kitchen with a central island, built-in appliances, and a breakfast bar.

A hotel room with a large bed, a television on a wooden dresser, a desk with a lamp, and a window with curtains.

8. Residence Inn by Marriott White Plains Westchester County

16.1 km from Pleasant Square

Nelson

$192

$220 total

includes taxes & fees

Sep 27 - Sep 28

A modern reception area with a wooden reception desk, a blue accent wall, and a large glass door leading to an outdoor seating area.

A modern breakfast bar with a variety of food options, including cereal and hot food. There are signs indicating breakfast and hot food availability.

An indoor swimming pool with a tiled floor, a ceiling with a grid pattern, and a view of greenery outside.

A hotel room with two beds, a blue sofa, a wooden coffee table, and a painting on the wall.

9. Holiday Inn Express & Suites Hawthorne Elmsford North by IHG

8.5 km from Pleasant Square

William

$148

$169 total

includes taxes & fees

Sep 20 - Sep 21

A modern hotel lobby with a kitchen area, seating arrangements, and large windows offering a view of the outdoors.

An indoor swimming pool with a glass ceiling, clear signage indicating depth, and lounge chairs along the sides.

A modern hotel lobby with a seating area, a kitchen, and a bar.

A hotel corridor with a patterned carpet, a railing, and a reception desk with a glass partition.

10. Baymont by Wyndham White Plains - Elmsford

10.9 km from Pleasant Square

Mohammad

$127

$145 total

includes taxes & fees

Sep 20 - Sep 21

An indoor swimming pool with clear glass ceilings, stone walls, and multiple lounge chairs around the pool area.

A hotel dining area with multiple tables and chairs, a bar with a counter and bar stools, and two televisions mounted on the wall.

A hotel room with a large bed, a bedside table with a lamp, a TV, and a bathroom with a mirror and sink.

A spacious lobby with a central seating area, a decorative wall, and a reception desk in the background.

11. DoubleTree by Hilton Hotel Nanuet

13.8 km from Pleasant Square

Maureen

$122

$142 total

includes taxes & fees

Sep 27 - Sep 28

A hotel with a modern facade, a prominent signage for SpringHill Suites Marriott, and a covered entrance area with seating.

A modern living room with two orange patterned armchairs, a glass coffee table, a flat-screen TV mounted above a fireplace, and a magazine on the table.

A hotel room with a flat-screen TV on a wooden dresser, a sofa, a bed with a white headboard, and two abstract paintings on the walls.

A hotel room with a bed, a desk with a chair, a TV, and artwork on the walls.

12. SpringHill Suites by Marriott Tarrytown Westchester County

11.2 km from Pleasant Square

Edward

$147

$168 total

includes taxes & fees

Sep 21 - Sep 22

A modern kitchen with a large island, bar stools, a flat-screen TV, and a stone backsplash.

A hotel room with a bed, a sofa, a nightstand, a lamp, and a framed picture on the wall.

A gym with treadmills, elliptical machines, and weightlifting equipment.

A snack and beverage vending area with a refrigerator and shelves stocked with various snacks and drinks.

13. Hampton Inn White Plains/Tarrytown

12 km from Pleasant Square

David

$118

$135 total

includes taxes & fees

Sep 20 - Sep 21

A modern kitchen with a central island, bar stools, a fireplace, and a contemporary pendant light.

A modern cafe with multiple seating options including tables, chairs, and sofas.

A courtyard with a fire pit, outdoor seating, and modern apartment buildings.

A modern interior with a dark wall, a wooden reception desk, a refrigerator stocked with beverages, shelves with snacks, and a large vase with orange flowers.

14. Courtyard by Marriott Tarrytown Westchester County

10.9 km from Pleasant Square

Brian

$169

$193 total

includes taxes & fees

Sep 27 - Sep 28

A modern bar area with a bar counter, multiple stools, and a seating area with a sofa and chairs.

A modern lounge with leather sofas, a patterned rug, and red pendant lights.

A modern dining area with a wooden table, cushioned seating, pendant lighting, and a large window offering a view of the outdoors.

15. Hotel Nyack, a JdV by Hyatt Hotel

9.5 km from Pleasant Square

John

$125

$171 total

includes taxes & fees

Sep 20 - Sep 21

A checkered floor, a potted plant, and two metal ladders in a room with large windows.

A hotel lobby with a sofa, armchairs, a glass table, and lamps.

A restaurant with a counter, stools, and a menu board.

A modern office space with a large desk, multiple printers, and comfortable seating.

16. West Gate Inn Nyack

9.6 km from Pleasant Square

Gareth

$99

$113 total

includes taxes & fees

Sep 15 - Sep 16

A spacious lobby with a red sofa, green armchairs, a fireplace, and a staircase leading to an upper level.

A spacious lobby with a red sofa set, a fireplace, and a staircase leading to an upper level.

A hotel entrance with a covered walkway, stone pillars, and potted plants.

An outdoor patio area with tables and chairs, red umbrellas, and flower planters.

17. Hotel MTK Mount Kisco

13.2 km from Pleasant Square

Andrea

$163

$187 total

includes taxes & fees

Sep 20 - Sep 21

A hotel room with a bed, two wall-mounted lamps, a round wooden table with a vase of flowers, and two framed pictures on the wall.

A street view with a Budget Motor Inn sign, a building with a beige facade, and a grassy area with a curb.

A building with a brown roof, a sign reading "OFFICE", and a parking sign with a 'B' indicating a parking bay.

A sign for the Budget Motor Inn with a vacancy notice.

18. Budget Motor Inn - Stony Point

12.3 km from Pleasant Square

Jody

$74

$82 total

includes taxes & fees

Sep 15 - Sep 16

A hotel room with a sofa, a coffee table, a TV, a desk, and a bed.

A coffee station with two coffee machines and a variety of coffee pods and cups.

A hotel room with a patterned sofa, a small ottoman, a desk with two chairs, a microwave, a wine bottle, and a framed picture on the wall.

A hotel room with two beds, a desk with a television, and a window with curtains.

19. Holiday Inn Express & Suites Peekskill-Lower Hudson Valley by IHG

14.4 km from Pleasant Square

Yael

$152

$174 total

includes taxes & fees

Oct 4 - Oct 5

A spacious hotel lobby with a modern design, featuring a large seating area, a dining table, and large windows providing views of the outdoors.

An outdoor patio with stone walls, a fire pit, and seating.

A modern kitchen with a central island, bar stools, wooden cabinets, and pendant lighting.

A large indoor swimming pool with clear glass walls, multiple lounge chairs, and ceiling lights.

20. Element by Marriott Spring Valley

14.8 km from Pleasant Square

Jed

$134

$156 total

includes taxes & fees

Oct 12 - Oct 13

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Other landmarks near Pleasant Square

Merchants Square

9.0/10 (2 reviews)

If you like spending time outside, why not spend the afternoon at Merchants Square, a park in the heart of Ossining. Why not take a stroll along the riverfront and watch the sunset while you're here? Want to stretch your legs some more? Head to Pleasant Square and Depot Square, both a short walk away.

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Sing Sing Prison Museum

If visiting museums in Ossining are on your list, you might want to check out the upcoming exhibitions at Sing Sing Prison Museum, located in the heart of town. Why not take a stroll along the riverfront and watch the sunset while you're here? If you want to see more of the museums in Ossining, Ossining Historical Society isn't far either.

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Ossining Public Library

If you're planning a bit of sightseeing during your trip, head to Ossining Public Library— just one of the monuments in central Ossining.

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Snowden Avenue Park

Snowden Avenue Park is worth a visit, located 0.3 mi (0.5 km) from central Ossining. Why not take a stroll along the riverfront and watch the sunset while you're here?

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Depot Square

Depot Square is 0.5 mi (0.8 km) from central Ossining, why not stop by during your stay. Why not take a stroll along the riverfront and watch the sunset while you're here? Want to stretch your legs some more? Head to Louis Engel Waterfront Park and Pleasant Square, both a short walk away.

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Nelson Park

Nelson Park is worth a visit, located 0.7 mi (1.2 km) from central Ossining. Why not take a stroll along the riverfront and watch the sunset while you're here?

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Crawbuckie Park

Crawbuckie Park is 0.7 mi (1.1 km) from central Ossining, why not stop by during your stay. Want to stretch your legs some more? Head to Croton Point Park and Rockland Lake State Park, both nearby.

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Louis Engel Waterfront Park

Louis Engel Waterfront Park is worth a visit, located 0.8 mi (1.3 km) from central Ossining. Why not take a stroll along the riverfront and watch the sunset while you're here?

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